PM3 semiempirical study and its comparison with X-ray crystal structure of 4-[2-Methyl-4-(4-methoxyphenylazo)] phenoxyphtalonitrile
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The molecular and crystal structures of the title compound, C22H16N4O2, were determined by single crystal X-ray diffraction technique. The title compound crystallizes in monoclinic space group P1 2 1 /n1, with a=12.7811(9) Å, b=8.2002(4) Å, c=17.8772(14) Å, Z=4, D calc=1.3112(1) g/cm3, μ (Mo-Kα)=0.087 mm−1. The structure was solved by direct methods and refined to a final R=0.056 for 1891 reflections with I > 2σ (I). The asymmetric unit in the crystal structure contains only one neutral molecule. The positions of nitrogen atoms in the azo groups were disordered. There is no classic hydrogen bond in the crystal structure. The molecules in the crystal structure are stacked by π–π stacking and one edge-to-face interactions. In order to determine conformational flexibility and crystal packing effects on the molecules, molecular energy profile of the title compound was obtained with respect to the selected torsion angle, which is varied from −180° to +180° in every 10° via PM3 semi-empirical method.
KEY WORDS:azo compound phtalonitrile; PM3 crystal structure conformational analysis.
Hasan Karabıyık would like to thank TÜBİTAK (The Scientific and Technical Research Council of Turkey) for partial financial support. In addition, the authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the STOE IPDS II diffractometer (purchased under grants F.279 and F.377 of the University Research Fund).
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